Deck 17: Carboxylic Acids

Question 1

What is the correct assignment of the names of the following substituted benzenes?

A) 1 = succinic acid; 2 = oxalic acid; 3 = malonic acid; 4 = adipic acid
B) 1 = oxalic acid; 2 = malonic acid; 3 = succinic acid; 4 = adipic acid
C) 1 = oxalic acid; 2 = succinic acid; 3 = adipic acid; 4 = malonic acid
D) 1 = adipic acid; 2 = malonic acid; 3 = succinic acid; 4 = oxalic acid

Answer 1

1 = oxalic acid; 2 = malonic acid; 3 = succinic acid; 4 = adipic acid

Question 2

Which of the following statements is not true regarding benzoic acid acids?

A) The neutral acid is the predominant species in aqueous solution at pH <2.
B) The anionic carboxylate is the predominant species in aqueous solution at pH >7.
C) Sodium benzoate is less soluble in water than benzoic acid.
D) Benzoic acid is extracted out of diethyl ether by treatment with aqueous sodium bicarbonate.

Answer 2

Sodium benzoate is less soluble in water than benzoic acid.

Question 3

Which of the following is the most soluble in water?

A) acetic acid
B) pentanol
C) butanoic acid
D) pentanal

Answer 3

acetic acid

Question 4

Which of the following has the highest boiling point?

A) hexane
B) 1-pentanol
C) pentanal
D) butanoic acid

Question 5

Which of the following is the correct order of decreasing acid strength (more acidic > less acidic)?

A) FCH₂COOH > ClCH₂COOH > BrCH₂COOH
B) CH₃COOH > ClCH₂COOH > Cl₂CHCOOH
C) CH₃COOH > FCH₂COOH > CH₃CH₂OH
D) CH₃CH₂OH > FCH₂COOH > ClCH₂COOH

Question 6

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 7

What is the approximate pK_a value of acetic acid

A) -2
B) 5
C) 15
D) 35

Question 8

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 9

What is the IUPAC name of the following compound?

A) cis-4-methylcyclohexanecarboxylic acid
B) trans-4-methylcyclohexanecarboxylic acid
C) cis-3-methylcyclohexanecarboxylic acid
D) trans-3-methylcyclohexanecarboxylic acid

Question 10

Which of the following is the most soluble in water?

A) hexane
B) 1-pentanol
C) pentanal
D) butanoic acid

Question 11

What is the IUPAC name of the following compound?

A) 4-methyl-3-phenyl-3-pentenoic acid
B) 4,4-dimethyl-3-phenyl-3-butenoic acid
C) 3-phenyl-2-methyl-2-penten-5-oic acid
D) (Z)-3-methyl-2-phenyl-2-butenoic acid

Question 12

What is the IUPAC name of the following compound?

A) (E)-4-ethyl-3-pentenoic acid
B) (Z)-4-ethyl-3-pentenoic acid
C) (E)-4-methyl-3-hexenoic acid
D) (Z)-4-methyl-3-hexenoic acid

Question 13

What is the IUPAC name of the following compound?

A) (2R,3R)-dihydroxybutanedioic acid
B) (2S,3S)-dihydroxybutanedioic acid
C) (2R,3S)-dihydroxybutanedioic acid
D) (2S,3R)-dihydroxybutanedioic acid

Question 14

What is the IUPAC name of the following compound?

A) 5,5-dimethyl-5-phenylpentanoic acid
B) 5-methyl-5-phenylhexanoic acid
C) 2,2-dimethylphenylpropanoic acid
D) 5,5-dimethyl-5-phenylbutanal

Question 15

What is the IUPAC name of the following compound

A) 3,3-dimethylhexanoic acid
B) 2,2-dimethylpentanoic acid
C) 2,2-dimethylpentanal
D) 4,4-dimethyl-6-hexanoyl acid

Question 16

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 17

What is the correct assignment of the names of the following substituted benzenes?

A) 1 = salicylic acid; 2 = benzoic acid; 3 = terephthalic acid; 4 = phthalic acid
B) 1 = terephthalic acid; 2 = salicylic acid; 3 = benzoic acid; 4 = phthalic acid
C) 1 = salicylic acid; 2 = terephthalic acid; 3 = phthalic acid; 4 = benzoic acid
D) 1 = phthalic acid; 2 = benzoic acid; 3 = terephthalic acid; 4 = salicylic acid

Question 18

Which of the following is the correct order of decreasing acid strength (more acidic > less acidic)?

A) FCH₂COOH > CH₃COOH > F₂CHCOOH
B) FCH₂COOH > CH₃COOH > CH₃OH
C) CH₃CH₂OH > ClCH₂COOH > BrCH₂COOH
D) CH₃COOH > ClCH₂COOH > CH₃OH

Question 19

Which of the following has the highest boiling point?

A) acetic acid
B) pentanol
C) butanoic acid
D) pentanal

Question 20

Which of the following is the correct order of decreasing acid strength (more acidic > less acidic)?

A) ICH₂COOH > ClCH₂COOH > FCH₂COOH
B) Cl₂CHCOOH > ClCH₂COOH > CH₃COOH
C) CH₃CH₂OH > FCH₂COOH > ClCH₂COOH
D) CH₃COOH > FCH₂COOH > CH₃CH₂OH

Question 21

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 22

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 23

What is the best choice of reagent to perform the following transformation?

A) NaCl
B) HCl
C) SOCl₂
D) Cl₂

Question 24

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 25

What is the best choice of reagent(s) to perform the following transformation?

A) CH₃OH, H₂SO₄
B) CH₃I, H₂SO₄
C) NaOCH₃
D) CH₃Li

Question 26

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 27

What is the best choice of reagent(s) to perform the following transformation?

A) 1. LiAlH₄; 2. H₃O⁺
B) H₂, Pt
C) 1. NaBH₄; 2. H₂O
D) NaH

Question 28

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 29

What is the best choice of reagent(s) to perform the following transformation?

A) 1. LiAlH₄; 2. H₃O⁺
B) H₂, Pt
C) 1. NaBH₄; 2. H₂O
D) NaH

Question 30

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 31

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 32

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 33

What is the best choice of reagent(s) to perform the following transformation?

A) 1. LiAlH₄; 2. H₃O⁺
B) H₂, Pt
C) 1. NaBH₄; 2. H₂O
D) NaH

Question 34

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 35

Which of the following is a reactive intermediate in the thermal decarboxylation of a 1,3-diacid?

A) enol
B) carbocation
C) carbanion
D) carboxylate

Question 36

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 37

What is the best choice of reagent(s) to perform the following transformation?

A) CH₃I, H₂SO₄
B) CH₃MgBr
C) LiOCH₃
D) CH₂N₂

Question 38

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 39

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 40

Which of the following carboxylic acids undergoes the most rapid thermal decarboxylation reaction?

A) 1
B) 2
C) 3
D) 4

Question 41

What is the major organic product obtained from the following reaction?

Question 42

What is the major organic product obtained from the following reaction?

Question 43

What is the major organic product obtained from the following reaction?

Question 44

What is the major organic product obtained from the following reaction?

Question 45

What is the major organic product obtained from the following reaction?

Question 46

Which of the following best describes the key mechanistic steps in the esterification of a carboxylic acid upon treatment with an alcohol in the presence of a strong acid?

A) addition followed by elimination
B) substitution followed by addition
C) elimination followed by addition
D) addition followed by decarboxylation

Question 47

What is the major organic product obtained from the following sequence of reactions?

Question 48

What is the major organic product obtained from the following reaction?

Question 49

What is the major organic product obtained from the following reaction?

Question 50

What is the major organic product obtained from the following reaction?

Question 51

What is the major organic product obtained from the following sequence of reactions?